Stewart Plus Two More
Never bring one option; show a Goldilocks three and hold the rest in the appendix.
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 3
- Confidence
- 90%
A structured way to present recommendations that proves you considered alternatives without drowning the exec in your homework. You lead with a point of view, offer roughly three options with the recommended one in the middle, and keep the fuller set of rejected options ready in an appendix in case they push back. Use it in any pitch or design review where you want alignment on a decision.
Origin
Fain names two Slack practices: 'Stewart plus two more,' where after Stewart Butterfield specified an exact design the team also built two alternatives they believed in, and a recovery with manager Rachel Woolen where a single-option doc failed and a two-day rewrite showing all considered permutations won approval. Lenny connects it to Barbara Minto's pyramid principle (recommendation first, then evidence).
Core principles
- 01Giving only one option makes the exec suspect you missed something; three options show deliberate consideration.
- 02The baseline expectation is that you did your homework, so proof belongs in the appendix, not the main flow.
- 03Presenting alternatives creates a forum to debate the merits of each approach rather than defending a single answer.
How to run it
- 1
Lead with the recommendation
Open with your point of view and why you believe it's the right one, rather than walking through your full process to a conclusion (the Minto pyramid, inverted from process-first storytelling).
Pro tip Match the format to the person; some execs want a doc with quiet reading time, some hate PowerPoint, some only want data.
- 2
Show three options with the middle as the pick
Present a Goldilocks set of three where your recommended solution sits in the middle, borrowing from pricing-and-packaging strategy, so the exec sees you weighed the space.
Pro tip The 'Stewart plus two more' variant: do exactly what the leader asked for, plus two alternatives you feel good about, to open a real conversation.
- 3
Keep the full option set in the appendix
Have the other permutations you considered ready in an appendix, a draft Figma file, or backup slides, so you can produce them the instant an exec asks 'how are you thinking about the permutations.'
Watch out Do NOT front-load all 15 options or every proof point; the exec who was most on the fence will glaze over and get on their phone.
In the wild
Fain's team brought a single-option strategy doc to a product review; CPO Rachel Woolen said she couldn't see how they were thinking about the permutations. They turned around a new doc in two days showing every option considered and why each did or didn't serve the outcomes.
→ Woolen then said 'I see why the solution that you're proposing makes the most sense,' and alignment followed.
Common mistakes
Showing too much work upfront
Parading '16 participants from 15 geos and statistically significant' proof to demonstrate diligence bores the exec and can blow the meeting.
Bringing a single option
Offering one answer reads as if you missed the alternatives and gives the exec nothing to align on.
Is it for you?
Best for
Product leaders seeking a decision or alignment from an exec who may probe the reasoning.
Not ideal for
Fast, low-stakes calls where an exec has explicitly asked for one clear recommendation and no options.
From the transcript
“give three options and the goldilocks in the middle is the perfect one”
“we called it Stuart plus two more. So, we did exactly what he asked for and then two other versions that we felt good about”
“It's not necessary to put all 15 options you considered, but at least be ready to show them”
From the episode
The art of influence: The single most important skill that AI can’t replace
Jessica Fain (Webflow, ex-Slack)